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In the mol­ecule of the title compound, [V(C11H7O2)O2(C12H8N2)]·0.25CH2Cl2, the central VV atom has an octa­hedral environment, with vanadyl and deprotonated phenol O atoms and two phenanthroline N atoms in the equatorial plane and vanadyl and aldehyde carbonyl O atoms in axial positions. In the crystal structure, inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions result in the formation of a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016741/hk2217sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016741/hk2217Isup2.hkl
Contains datablock I

CCDC reference: 639896

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.012 Å
  • Disorder in solvent or counterion
  • R factor = 0.093
  • wR factor = 0.302
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.302 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio PLAT084_ALERT_2_C High R2 Value .................................. 0.30 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C24 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12 PLAT411_ALERT_2_C Short Inter H...H Contact H10 .. H24A .. 2.14 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl2 .. C24 .. 3.21 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C24 .. C24 .. 3.19 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(1-Formyl-2-naphtholato-κ2O,O')dioxo(1,10-phenanthroline- κ2N,N')vanadium(V) dichloromethane quatersolvate top
Crystal data top
[V(C11H7O2)O2(C12H8N2)]·0.25CH2Cl2F(000) = 930
Mr = 455.54Dx = 1.402 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1548 reflections
a = 13.860 (2) Åθ = 2.4–25.3°
b = 7.3946 (14) ŵ = 0.55 mm1
c = 21.063 (2) ÅT = 298 K
β = 90.105 (2)°Block, yellow
V = 2158.8 (6) Å30.23 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
3770 independent reflections
Radiation source: fine-focus sealed tube1689 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.883, Tmax = 0.922k = 68
10232 measured reflectionsl = 2524
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.302H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.1784P)2]
where P = (Fo2 + 2Fc2)/3
3770 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.96 e Å3
24 restraintsΔρmin = 0.72 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
V10.69966 (10)0.35006 (18)0.63224 (6)0.0649 (5)
N10.6243 (5)0.3105 (7)0.5438 (3)0.0585 (16)
N20.5465 (5)0.2605 (8)0.6576 (3)0.0618 (16)
O10.7038 (4)0.0555 (8)0.6263 (2)0.0790 (16)
O20.7294 (4)0.3058 (7)0.7188 (3)0.0713 (15)
O30.8047 (4)0.3515 (9)0.5978 (3)0.0908 (19)
O40.6664 (4)0.5577 (7)0.6381 (2)0.0763 (16)
Cl10.8973 (15)0.640 (2)0.5323 (10)0.211 (8)0.25
Cl20.8606 (11)1.026 (2)0.5153 (9)0.190 (7)0.25
C10.7493 (6)0.0455 (12)0.6626 (4)0.071 (2)
H10.75490.16580.65020.085*
C20.7940 (5)0.0025 (10)0.7214 (3)0.0575 (18)
C30.7764 (5)0.1737 (10)0.7478 (4)0.063 (2)
C40.8082 (6)0.2053 (12)0.8125 (4)0.073 (2)
H40.79570.31630.83150.087*
C50.8554 (6)0.0769 (12)0.8454 (4)0.074 (2)
H50.87330.10050.88710.089*
C60.8785 (5)0.0922 (12)0.8186 (4)0.069 (2)
C70.8498 (5)0.1331 (10)0.7561 (3)0.0597 (19)
C80.8762 (6)0.3021 (11)0.7310 (4)0.074 (2)
H80.85810.33050.68970.088*
C90.9265 (6)0.4237 (13)0.7646 (5)0.080 (2)
H90.94280.53450.74670.096*
C100.9545 (7)0.3827 (14)0.8272 (5)0.093 (3)
H100.99010.46700.85010.111*
C110.9308 (7)0.2235 (14)0.8550 (5)0.089 (3)
H110.94810.19990.89680.107*
C120.6619 (6)0.3395 (11)0.4860 (4)0.073 (2)
H120.72600.37620.48390.088*
C130.6136 (7)0.3195 (11)0.4302 (4)0.078 (2)
H130.64410.33860.39150.093*
C140.5175 (7)0.2697 (11)0.4331 (4)0.078 (2)
H140.48230.25690.39570.093*
C150.4721 (6)0.2382 (10)0.4919 (4)0.0632 (19)
C160.5288 (5)0.2610 (9)0.5464 (3)0.0552 (18)
C170.4876 (5)0.2360 (9)0.6071 (3)0.0564 (18)
C180.3896 (6)0.1872 (9)0.6134 (4)0.064 (2)
C190.3537 (7)0.1623 (11)0.6748 (5)0.083 (3)
H190.28970.12930.68100.100*
C200.4129 (7)0.1866 (12)0.7247 (5)0.087 (3)
H200.38960.17120.76570.104*
C210.5108 (7)0.2355 (12)0.7151 (4)0.078 (2)
H210.55080.25040.75020.093*
C220.3744 (6)0.1911 (11)0.4991 (5)0.079 (2)
H220.33590.17740.46330.095*
C230.3355 (7)0.1654 (11)0.5570 (5)0.081 (3)
H230.27100.13210.55990.097*
C240.9271 (14)0.857 (2)0.5301 (11)0.24 (4)0.25
H24A0.95560.88180.57120.293*0.25
H24B0.97950.86430.49970.293*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0704 (10)0.0625 (9)0.0618 (9)0.0084 (7)0.0102 (7)0.0026 (6)
N10.065 (4)0.056 (4)0.055 (4)0.001 (3)0.008 (3)0.002 (3)
N20.080 (4)0.058 (4)0.048 (3)0.003 (3)0.000 (3)0.008 (3)
O10.090 (4)0.074 (4)0.073 (4)0.004 (3)0.027 (3)0.010 (3)
O20.075 (4)0.063 (3)0.076 (4)0.005 (3)0.022 (3)0.009 (3)
O30.056 (3)0.120 (5)0.096 (4)0.013 (3)0.004 (3)0.005 (4)
O40.115 (4)0.050 (3)0.064 (3)0.012 (3)0.017 (3)0.000 (2)
Cl10.203 (11)0.230 (11)0.202 (11)0.041 (9)0.019 (9)0.068 (9)
Cl20.193 (10)0.195 (11)0.183 (10)0.009 (8)0.008 (8)0.022 (8)
C10.072 (5)0.069 (5)0.073 (5)0.001 (4)0.022 (4)0.003 (4)
C20.050 (4)0.061 (5)0.061 (4)0.002 (3)0.009 (3)0.003 (4)
C30.059 (5)0.067 (5)0.061 (5)0.000 (4)0.016 (4)0.009 (4)
C40.076 (6)0.078 (6)0.064 (5)0.003 (4)0.009 (4)0.007 (4)
C50.078 (6)0.082 (6)0.063 (5)0.002 (5)0.016 (4)0.006 (4)
C60.055 (5)0.086 (6)0.067 (5)0.003 (4)0.011 (4)0.010 (4)
C70.044 (4)0.070 (5)0.065 (5)0.006 (4)0.006 (3)0.001 (4)
C80.062 (5)0.070 (6)0.089 (6)0.001 (4)0.002 (4)0.001 (4)
C90.068 (6)0.075 (6)0.097 (7)0.013 (4)0.008 (5)0.004 (5)
C100.075 (6)0.092 (7)0.112 (8)0.016 (5)0.015 (6)0.020 (6)
C110.087 (7)0.092 (7)0.088 (6)0.015 (5)0.014 (5)0.010 (5)
C120.072 (5)0.071 (6)0.076 (6)0.003 (4)0.011 (5)0.007 (4)
C130.097 (7)0.084 (6)0.052 (5)0.009 (5)0.005 (5)0.002 (4)
C140.103 (7)0.075 (6)0.055 (5)0.016 (5)0.014 (5)0.008 (4)
C150.078 (6)0.055 (5)0.057 (5)0.004 (4)0.017 (4)0.004 (4)
C160.067 (5)0.045 (4)0.054 (4)0.001 (3)0.004 (4)0.001 (3)
C170.065 (5)0.047 (4)0.057 (4)0.003 (3)0.004 (4)0.000 (3)
C180.062 (5)0.052 (5)0.078 (5)0.003 (3)0.000 (4)0.003 (4)
C190.080 (6)0.065 (6)0.105 (7)0.004 (4)0.017 (6)0.008 (5)
C200.092 (7)0.081 (7)0.087 (7)0.003 (5)0.030 (6)0.009 (5)
C210.103 (7)0.074 (6)0.056 (5)0.001 (5)0.001 (5)0.000 (4)
C220.074 (6)0.073 (6)0.091 (7)0.003 (4)0.024 (5)0.009 (5)
C230.067 (6)0.073 (6)0.102 (7)0.011 (4)0.014 (5)0.000 (5)
C240.25 (4)0.25 (4)0.24 (4)0.000 (11)0.003 (11)0.008 (11)
Geometric parameters (Å, º) top
V1—O12.182 (6)C9—C101.407 (12)
V1—O21.896 (6)C9—H90.9300
V1—O31.627 (6)C10—C111.355 (13)
V1—O41.608 (5)C10—H100.9300
V1—N12.153 (6)C11—H110.9300
V1—N22.287 (6)C12—C131.359 (11)
N1—C121.344 (9)C12—H120.9300
N1—C161.375 (9)C13—C141.384 (12)
N2—C211.324 (9)C13—H130.9300
N2—C171.352 (9)C14—C151.409 (11)
O1—C11.240 (9)C14—H140.9300
O2—C31.323 (9)C15—C161.400 (10)
Cl1—C241.659 (15)C15—C221.408 (11)
Cl2—C241.583 (19)C16—C171.413 (9)
C1—C21.428 (10)C17—C181.412 (10)
C1—H10.9300C18—C191.397 (12)
C2—C31.404 (10)C18—C231.412 (11)
C2—C71.460 (10)C19—C201.345 (13)
C3—C41.451 (10)C19—H190.9300
C4—C51.345 (11)C20—C211.418 (12)
C4—H40.9300C20—H200.9300
C5—C61.409 (11)C21—H210.9300
C5—H50.9300C22—C231.347 (12)
C6—C71.409 (10)C22—H220.9300
C6—C111.432 (11)C23—H230.9300
C7—C81.405 (10)C24—H24A0.9700
C8—C91.339 (11)C24—H24B0.9700
C8—H80.9300
O2—V1—O182.9 (2)C10—C9—H9120.2
O3—V1—O187.6 (3)C11—C10—C9121.6 (9)
O4—V1—O1164.8 (3)C11—C10—H10119.2
N1—V1—O180.1 (2)C9—C10—H10119.2
O3—V1—O2103.7 (3)C10—C11—C6118.8 (9)
O4—V1—O298.8 (2)C10—C11—H11120.6
O4—V1—O3106.5 (3)C6—C11—H11120.6
O2—V1—N1155.8 (2)N1—C12—C13125.1 (8)
O3—V1—N192.8 (3)N1—C12—H12117.4
O4—V1—N193.3 (2)C13—C12—H12117.4
O1—V1—N275.5 (2)C12—C13—C14117.6 (8)
O2—V1—N285.8 (2)C12—C13—H13121.2
O3—V1—N2159.5 (3)C14—C13—H13121.2
O4—V1—N289.6 (3)C13—C14—C15120.9 (8)
N1—V1—N273.4 (2)C13—C14—H14119.5
C12—N1—C16117.0 (7)C15—C14—H14119.5
C12—N1—V1125.1 (6)C16—C15—C22118.6 (8)
C16—N1—V1117.9 (4)C16—C15—C14116.8 (8)
C21—N2—C17118.3 (7)C22—C15—C14124.5 (8)
C21—N2—V1127.1 (6)N1—C16—C15122.5 (7)
C17—N2—V1114.5 (5)N1—C16—C17117.5 (6)
C1—O1—V1125.4 (5)C15—C16—C17119.9 (7)
C3—O2—V1132.6 (5)N2—C17—C18122.8 (7)
O1—C1—C2127.1 (8)N2—C17—C16116.7 (7)
O1—C1—H1116.4C18—C17—C16120.6 (7)
C2—C1—H1116.4C19—C18—C17117.6 (8)
C3—C2—C1119.4 (7)C19—C18—C23125.0 (9)
C3—C2—C7120.9 (7)C17—C18—C23117.3 (8)
C1—C2—C7119.4 (7)C20—C19—C18119.2 (9)
O2—C3—C2124.7 (7)C20—C19—H19120.4
O2—C3—C4117.6 (7)C18—C19—H19120.4
C2—C3—C4117.7 (7)C19—C20—C21120.3 (8)
C5—C4—C3121.1 (8)C19—C20—H20119.8
C5—C4—H4119.4C21—C20—H20119.8
C3—C4—H4119.4N2—C21—C20121.7 (8)
C4—C5—C6122.1 (8)N2—C21—H21119.1
C4—C5—H5118.9C20—C21—H21119.1
C6—C5—H5118.9C23—C22—C15121.3 (8)
C5—C6—C7120.0 (7)C23—C22—H22119.3
C5—C6—C11120.2 (8)C15—C22—H22119.3
C7—C6—C11119.8 (9)C22—C23—C18122.2 (8)
C8—C7—C6117.9 (7)C22—C23—H23118.9
C8—C7—C2124.1 (7)C18—C23—H23118.9
C6—C7—C2118.0 (7)Cl2—C24—Cl1128.7 (16)
C9—C8—C7122.3 (9)Cl2—C24—H24A105.1
C9—C8—H8118.8Cl1—C24—H24A105.1
C7—C8—H8118.8Cl2—C24—H24B105.1
C8—C9—C10119.6 (9)Cl1—C24—H24B105.1
C8—C9—H9120.2H24A—C24—H24B105.9
O4—V1—N1—C1289.7 (6)C3—C2—C7—C8175.3 (7)
O3—V1—N1—C1217.0 (6)C1—C2—C7—C810.7 (11)
O2—V1—N1—C12150.2 (6)C3—C2—C7—C65.0 (10)
O1—V1—N1—C12104.1 (6)C1—C2—C7—C6169.0 (7)
N2—V1—N1—C12178.3 (6)C6—C7—C8—C90.5 (12)
O4—V1—N1—C1686.7 (5)C2—C7—C8—C9179.2 (8)
O3—V1—N1—C16166.6 (5)C7—C8—C9—C100.1 (13)
O2—V1—N1—C1633.4 (8)C8—C9—C10—C110.9 (14)
O1—V1—N1—C1679.6 (5)C9—C10—C11—C62.0 (14)
N2—V1—N1—C161.9 (5)C5—C6—C11—C10178.0 (8)
O4—V1—N2—C2187.1 (7)C7—C6—C11—C102.3 (13)
O3—V1—N2—C21130.4 (9)C16—N1—C12—C131.7 (11)
O2—V1—N2—C2111.7 (6)V1—N1—C12—C13178.0 (6)
N1—V1—N2—C21179.3 (7)N1—C12—C13—C141.7 (13)
O1—V1—N2—C2195.5 (7)C12—C13—C14—C151.0 (12)
O4—V1—N2—C1791.2 (5)C13—C14—C15—C160.4 (11)
O3—V1—N2—C1751.4 (10)C13—C14—C15—C22178.6 (8)
O2—V1—N2—C17170.0 (5)C12—N1—C16—C151.0 (10)
N1—V1—N2—C172.4 (5)V1—N1—C16—C15177.6 (5)
O1—V1—N2—C1786.2 (5)C12—N1—C16—C17177.9 (6)
O4—V1—O1—C1122.3 (10)V1—N1—C16—C171.3 (8)
O3—V1—O1—C179.3 (7)C22—C15—C16—N1178.7 (7)
O2—V1—O1—C124.8 (7)C14—C15—C16—N10.4 (10)
N1—V1—O1—C1172.6 (7)C22—C15—C16—C170.2 (10)
N2—V1—O1—C1112.2 (7)C14—C15—C16—C17178.5 (7)
O4—V1—O2—C3166.6 (7)C21—N2—C17—C180.8 (10)
O3—V1—O2—C357.1 (7)V1—N2—C17—C18177.6 (5)
N1—V1—O2—C374.4 (9)C21—N2—C17—C16179.0 (7)
O1—V1—O2—C328.7 (7)V1—N2—C17—C162.6 (8)
N2—V1—O2—C3104.5 (7)N1—C16—C17—N21.0 (9)
V1—O1—C1—C211.8 (12)C15—C16—C17—N2179.9 (6)
O1—C1—C2—C39.6 (12)N1—C16—C17—C18179.2 (6)
O1—C1—C2—C7176.3 (8)C15—C16—C17—C180.3 (10)
V1—O2—C3—C218.8 (12)N2—C17—C18—C190.6 (11)
V1—O2—C3—C4164.0 (5)C16—C17—C18—C19179.2 (7)
C1—C2—C3—O28.3 (12)N2—C17—C18—C23179.9 (7)
C7—C2—C3—O2177.7 (7)C16—C17—C18—C230.1 (10)
C1—C2—C3—C4168.9 (7)C17—C18—C19—C200.5 (11)
C7—C2—C3—C45.2 (11)C23—C18—C19—C20179.7 (8)
O2—C3—C4—C5179.3 (7)C18—C19—C20—C210.5 (13)
C2—C3—C4—C51.9 (12)C17—N2—C21—C200.8 (11)
C3—C4—C5—C61.6 (13)V1—N2—C21—C20177.4 (6)
C4—C5—C6—C71.8 (13)C19—C20—C21—N20.7 (13)
C4—C5—C6—C11178.6 (8)C16—C15—C22—C230.9 (12)
C5—C6—C7—C8178.8 (7)C14—C15—C22—C23179.1 (8)
C11—C6—C7—C81.6 (11)C15—C22—C23—C181.2 (13)
C5—C6—C7—C21.5 (11)C19—C18—C23—C22179.8 (8)
C11—C6—C7—C2178.1 (7)C17—C18—C23—C220.6 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O4i0.932.413.199 (10)143
C14—H14···O4ii0.932.573.219 (11)126
C20—H20···O4iii0.932.323.237 (11)166
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y1/2, z+3/2.
 

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